Search Results: worried about his past

Backstory: So I'm 24. I went to high school with this guy a few years back (we'll call him Matt) and we were best friends in high school. He was always interested in me, asking me out, and we went out a lot and spend tons of time together. Made each other laugh till we cried, and were just always there for each other. We were super close for 4 years, and I went to college and we fell out of touch (my fault). He texted me 5 years ago out of the blue, and all the feelings came rushing back. We had dinner a few times, and he asked me multiple times over the past few years to hang out, but I didn't because I'm just an idiot and I have no excuse really.

Long story short, I realized I loved him and still do, but haven't had the courage to tell him after all these years of feeling this way. He now has a serious girlfriend, they've been dating for a year, and seem super happy together. I'm worried that they'll get engaged and I'll never get to tell him how I feel. You should know what I've been in a 6-year relationship that has been HAUNTED by Matt, I can't stop thinking about him, I even have dreams about him, regularly! Super weird. Truth is, I just miss him like hell and I still love him, and I wouldn't be able to live with myself if he got engaged or married and I never told him. Problem is, I don't want to ruin his relationship or disrespect him in any way by telling him how I feel. So guys... should I tell him?

So there's this "friend".. I do want to have sex with him and he knows since I've told him a handfull amount of times. But with condoms or at least be on the pill... Which i am not but was planning to be.
Im from a good neighborhood but he's street grown.. Therefore he's used to easy girls only. he's 19 and im 23.. I dont do one nights and had only 2 partners before.. He slept with over 20 girls.. Just giving you guys our personality's background. Yesturday he invited me over, and when i entered his place the lights were off.. i asked why? He said "my curtains are see tru" :/.. And took me RIGHT AWAY to his bed.. Lol.. To cuddle and ground on me.. Which i love.. BUT it went down later on.. He tried to put it in and i said, for the 15th time, we need protection (i prefer condoms givong his past) and refused.. Again we spoke of that already.
Then he was fingering me and went down on me and kept fighting for the same thing, but i kept saying no (giving his past, i didn't tell him that his past was the reason.. Worried to insult him.. I just said it for pregnancy). He then turned me over and i had to put my hand over my vagina since i couldnt see anymore what he was doing and got supposedly super insulted. He said "i feel like im rapping you if you're putting your hand there" he burried his face in his pillow. i guess he felt rejected and embarassed so i spent the next 10 minutes boosting his ego because i felt bad for making him feel bad. I told him how much he turns me on and i really like him etc etc.. He decided to come back to me again but only to do the same thing. his dick was out going towards my vagina so i had to out my hand again. he then said that all of that was really weird and wack and he wanted to go to sleep. He gave a weird vibe.. He was covering his face again.. I kept explaining to him that its not him, its pregnancy that scares me.. He is a very insecured guy i think, he didn't want to show me his penis (its good size and nice, i saw for 3 seconds)

I've been with my boyfriend for two and a half years now, but in the beginning of our relationship, he had cheated on me with a girl more than once. I still see pics of this girl on social media because we have mutual friends and I get so upset every time I think about it. What makes it worse is that we're doing long distance now and I fear he'll cheat again. He's shown me that he loves me and I've met everyone at his college so I'm less worried. Although, I always feel like I'll never get past him cheating before.